Chester Hill Holidays from AU$445

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Your Chester Hill Holiday

Make planning your travels simple by booking a holiday package to Chester Hill. We'll take care of the minutiae, so you can focus on savouring everything this neighbourhood has to offer. Not sure what to do and see during your trip to Chester Hill? Nearby attractions like Auburn Botanic Gardens, Crest Sporting Complex and Crest of Bankstown Reserve are good places to begin. Whatever your travel goals or budget, booking your perfect Chester Hill holiday is quick and easy with Expedia.

Top Holiday Package Deals in Chester Hill

Price found within the past 48 hours. Click for updated prices.
Haven Glebe

Haven Glebe

4.5 out of 5
Glebe
Save 100% on your flight
Price was AU$738, price is now AU$445 per person
AU$445
per person
15 Jan - 18 Jan
found 1 day ago
Return flight included
Melbourne (AVV) to Sydney (SYD)
8.8/10 Excellent! (969 reviews)
Parking was easy and safe. Staff very friendly and helpful. The location was great with shops across the road.

Reviewed on 16 Oct 2025

Brokenback Views Country Estate

Brokenback Views Country Estate

3.5 out of 5
Save 100% on your flight
Price was AU$1,313, price is now AU$745 per person
AU$745
per person
2 Dec - 6 Dec
found 1 day ago
Return flight included
Melbourne (AVV) to Sydney (SYD)
9/10 Wonderful! (28 reviews)
Quiet area centrally located Peaceful views Would have wanted more towels for 2 nights Fireplace would have totally set it to perfection

Reviewed on 19 May 2024

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Save 100% on your flight
Price was AU$1,535, price is now AU$936 per person
AU$936
per person
6 Jan - 10 Jan
found 2 hours ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
9.2/10 Wonderful! (1,009 reviews)
Great staff and amenities but I could seem to have much control over the room temperature.

Reviewed on 30 Oct 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$847, price is now AU$529 per person
AU$529
per person
6 Jan - 8 Jan
found 1 day ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.2/10 Very Good! (1,009 reviews)
Nice staff and clean rooms.

Reviewed on 22 Oct 2025

The Sebel Quay West Suites Sydney

The Sebel Quay West Suites Sydney

5 out of 5
The Rocks
Save 100% on your flight
Price was AU$2,021, price is now AU$1,286 per person
AU$1,286
per person
21 Jan - 28 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
9.2/10 Wonderful! (2,369 reviews)
I love the fact that part of the hotel overlooked the Sydney Harbour and the Opera House. It was beautiful.

Reviewed on 21 Oct 2025

Our guide on where to stay in Chester Hill

Find the best Chester Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chester Hill
Default Image

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(8,551 area reviews)

Known for its captivating waterfront views and popular shops, there's plenty to explore in Sydney Central Business District. Check out top attractions like Circular Quay and Sydney Opera House, and jump on the metro at Martin Place Station or St. James Station to see more of the city.

Find hotels in Sydney Central Business District

Our pick of the best Chester Hill Hotel Deals

Shangri-La Sydney

Shangri-La Sydney

5 out of 5
176 Cumberland Street, The Rocks, NSW
The price is AU$326 per night from 9 Nov to 10 Nov
AU$326
9 Nov - 10 Nov
includes taxes & fees
9/10 Wonderful! (2,414 reviews)
-

Reviewed on 29 Oct 2025

Shangri-La Sydney
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
199 George St., Sydney, NSW
Fully refundableReserve now, pay when you stay
The price is AU$396 per night from 9 Nov to 10 Nov
AU$396
9 Nov - 10 Nov
includes taxes & fees
9.6/10 Exceptional! (1,985 reviews)
The room was more than we expected. The staff were very friendly and polite.

Reviewed on 29 Oct 2025

Four Seasons Hotel Sydney
View Sydney

View Sydney

4 out of 5
17 Blue Street, North Sydney, NSW
Fully refundableReserve now, pay when you stay
The price is AU$245 per night from 2 Nov to 3 Nov
AU$245
2 Nov - 3 Nov
includes taxes & fees
9/10 Wonderful! (1,169 reviews)
Amazing views!
Room climate was perfect!

Reviewed on 27 Oct 2025

View Sydney
See all 5,742 properties in Chester Hill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chester Hill holiday package cost?
Be ready to book, because a trip to Chester Hill starts from an enticing AU$445. When you combine your flights, hotels and car rentals into a package, you'll land the biggest bargains.
How do I get a cheap travel package to Chester Hill?
Combining your flight and hotel with Expedia won't just save you time — it'll save you money too. A Chester Hill holiday package makes it simple to arrange your perfect trip. With more than 550 airlines across the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1 000 000 hotel options globally to take your pick of. Now that's what you call choice. No matter who you are, Expedia puts the world within your reach.
Where should I stay in Chester Hill?
Most who travel to Chester Hill put both Sydney Opera House and Sydney Harbour Bridge on their sightseeing itineraries. Why not select a hotel close to one of these great attractions?
What are the top hotels in Chester Hill?
When it comes to comfy and convenient places to stay in Chester Hill, you can't beat Nightcap at Chester Hill Hotel. Browse its deals and pick up a bargain.
How far in advance should I book my Chester Hill holiday?
Search Expedia to compare international flights ASAP. You can generally purchase a seat up to a year before departure. If it's too early for your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to Chester Hill sometimes appear just weeks before departure.
What does an Expedia Chester Hill travel package include?
Rental cars, flights and hotels — we have them well covered. With Expedia, you can shape your Chester Hill travel package the way you want. All you have to do is work out what you need. Once you've made your booking, you can add extras like tours and activities. The more you bundle, the bigger the savings!
What should I know before booking a Chester Hill travel package?
Get set to save with an Expedia travel package. Bundle your airfares, rental cars and hotels and enjoy terrific discounts. Hotels aren't your only option, though. Book with us and take your pick of beachfront villas, chalets in the middle of mountains and even castles and houseboats!
Can I choose my airline with a Chester Hill Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're looking to fly to Chester Hill in economy or first class, simply select from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Chester Hill holiday package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Chester Hill holiday package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to find out more.

Discover the most popular places to visit in Chester Hill

Circular Quay showing street scenes, a city and a sunset

Circular Quay

4.5/5(4,882 reviews)

Under the gaze of the magnificent Opera House and Harbour Bridge, Sydney’s transport hub is a terminal of unexpected beauty.

Circular Quay
Sydney Opera House

Sydney Opera House

4.5/5(3,486 reviews)

Take in a performance or just take in the splendour of one of the world’s most famous buildings.

Sydney Opera House
Sydney Harbour Bridge

Sydney Harbour Bridge

4.5/5(3,601 reviews)

An iconic structure on a beautiful harbour with breath-taking views at any time of day or night. Climb it, walk it, photograph it or just stand back and admire it.

Sydney Harbour Bridge

Activities

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

AU$54
per adult
84% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

AU$30
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise

AU$85
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
See all activities in Sydney
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.